How to Plan a Solo Trip You'll Actually Enjoy

We plan our trips around the famous sights, the must-do list, the things we'd feel a little silly skipping. And then we come home exhausted, having seen everything without focusing on enjoyment.

What if the trip you'll actually enjoy is the one you subtract down to yourself? Think about the best afternoon you've ever had on a trip. I'd bet it wasn't the landmark everyone photographs. It might even be something you'd never have written on an itinerary, and you still think about it months later with a smile.

This episode is about how to plan a solo trip around the woman who is actually going, not the one you think you should be, and it doesn't start with where to go but with a better question that prioritizes your enjoyment.

We focus on a trip built for delight instead of for more, more, more, and the simple reason a choice that genuinely fits you, what psychologists call self-concordant, is the one you put more into and get more back out of.

In this episode:

- The afternoon that wasn't on the list
- The myth of the one right trip
- The subtraction effect
- Being good company for yourself
- The Krakow evening I skipped the sights
- One swap before you go

This episode is for you if:

• You've decided you want to travel solo and the planning advice you keep finding feels like it's written for somebody else
• You're worried you'll do everything right, see all the right sights, and still come home feeling like you didn't really enjoy it
• You keep a famous landmark on the itinerary just because you'd feel silly skipping it, even though you don't actually want to go
• You're a woman over 40 who wants a trip that fits the woman you are now, not a twenty-two-year-old backpacker with no preferences
• You already travel solo, or you want to, and you're ready for the how

About Freedom Looks Like This:

Freedom Looks Like This is a podcast for women over 40 who want to travel solo, or who already do, and want to go deeper. Host Damianne President explores self-trust, decision-making, and what it actually takes to stop waiting and give yourself permission to start moving. New episodes every Tuesday. For solo female travelers, midlife women, and anyone who suspects that the real barrier isn't logistics.

Transcript

SPEAKER_00 0:00

I want you to think for a moment about the best afternoon you've ever had on a trip. I'd be willing to bet that it was not the most famous site you went to visit because those tend to be crowded with lots of people. Maybe you got lost in a new city and stumbled upon something unexpected, or you got to linger over a cup of coffee or a pot of tea with no worries at all for the day. These are the memories that you may find yourself thinking about months or even years later with a smile. Did you know that you can design a whole trip around afternoons like that on purpose? That's what we're talking about in this episode. Stay with me if you're thinking about taking a trip on your own and you want to make it suit you. Most women think solo travel is about being brave or fearless, but it's really about letting go of the expectations holding you in place. This show is about what changes when you stop waiting and take yourself seriously, starting with intentional travel. I'm Demianne, and this is Rhino Looks Like This. Let's get started. I want to take you to an afternoon in Osaka because I'd booked myself an afternoon tea, and I'll tell you up front that I will always choose afternoon tea if I can. I've done afternoon teas in lots of countries around the world. It's one of my favorite things to do by myself when I travel. And on this particular day, I was running a little bit behind because I'd been working and I'd taken a break in the middle of the day, kind of like a lunch break to go for afternoon tea. So I was a bit harried walking there, feeling like the clock was ticking, and I definitely did not want to be late. And here's the thing: I could have taken a train or even a taxi, and it would have been faster, especially since my time was already crunched, that I wanted to walk. And so I did. And I gave myself that, even though I was feeling a bit flustered, because the walk was part of what I'd actually wanted to experience that afternoon. And that was more important to me than saving a little bit of time. So I got there and was thoroughly welcomed. And when I finally sat down, that flustered feeling just rained out of me. I was seated where I could look out onto a little garden, and the service was impeccable. If you've been to Japan, you know what I'm talking about. It's the kind of service where you feel like they're genuinely happy that you're there. And I love those small, careful touches, the attention to detail. So, for example, as the sun was shining and encroaching more and more into the restaurant, once it got to the tables, a waiter came over and lowered the blinds just enough so that the table was completely shaded. And the food was delightful. Although it was an afternoon tea, it was also like a cross menu because I was served soup and there was a salad and there was even some seafood. So while I enjoyed the flavors, I also enjoyed the spectacle, the presentation. There was more than I could eat, and I didn't try to finish everything, but I did enjoy every minute of what I ate. And mostly I just sat there and I watched the people, I watched the environment, I watched how everything moved through the space. That afternoon tea is such a strong memory for me. There were so many textures and tastes and flavors and sounds, just listening to everyone. And I have some other memories of afternoons just like this. It wasn't a famous building. I don't know if the restaurant was famous. I went there because they offered a strawberry afternoon tea. But really, there was nothing that I could point to and say, Have you seen this? It was the walk, the view of the garden, the table, the food. And it was one of my best afternoons of the trip. I've come to believe that there isn't one right trip. There isn't a perfect, correct itineraristic out there that you're supposed to find and book. And if you just research hard enough, you'll find it. What's right depends on the season that you're in. And it also depends on the moment. The trip for me a few years ago is not the right trip for me now. And the right afternoon on day one is not necessarily the right afternoon on day four. So for me, right is much more about tuning into the moment and recognizing how it's going. It's about being able to feel my feelings and not be afraid of them or avoid them. So some right days it's afternoon tea in London or in Cape Town or in Osaka. And some days rising is realizing that there's an invitation in front of you, some new friends, a plan that's already in motion. And the right thing is to say yes to that instead. So when people ask me how to plan a solo trip you'll actually enjoy, this is where I start. It's really not about having a list of sites to get through. Intentional solo travel is all about being with yourself. It's the same as when you take a trip with a good friend because you want to spend time with her and you want to get to know her better. You're doing the same thing with yourself. So the whole trip is the company you're keeping with you. So I look for opportunities to laugh with myself or sometimes at myself. And if there's something that I would point out or share to somebody else, I'm intentional about noticing it. Because if it's something that I can laugh at with a friend, why can't I laugh at it even by myself? So I want to catch these moments where I would normally hold back from enjoying something out loud just because there's no one next to me. And I want to let myself enjoy it anyway. That's what being good company for yourself looks like. And once you see it that way, the idea about planning a trip changes. Because if the trip is time with yourself, then the test of a good plan or a good trip isn't did I see everything? The test is, did I enjoy the company? Did I want to be there? And these are completely different questions. And they build completely different trips. Psychologists actually have a name for this. Okay, I know you don't need the name, but I'm a bit of a geek and I like digging into the explanation for things. When a choice really fits who you are, your own values and your interests, it's called self-concordant. Now that's a mouthful. But what they find is simple. When something fits you like that, you put more of yourself into it and you get more back out of it. So that's the whole difference between an afternoon you chose and an afternoon where you just endured it. So if you take nothing else from this episode, I want you to remember this. Planning a trip is about design, not logistics. You design it for the woman who is actually going. And the way you do that is by subtracting, taking out everything that's only there because you think you should. And then you judge the plan by one question. That question is not, did I see everything? It's did I want to be there? I don't think you need me to tell you or convince you what kind of trip would be good. If you've already decided you want to go on a trip, you've already given yourself some indication that the trip will be good. But what you need is a way to plan it so that it doesn't betray your intentions. That's where a lot of planning can go wrong. Maybe you open the search or you're browsing social media, and within a few minutes, you have a long list of all of the things you're supposed to do in this place. The things that will give you the beautiful photos, the famous landmarks, maybe the walking tour everyone rates as a five. Maybe there's a day trip that everyone says it's just wonderful and you'd feel silly if you skipped it. But none of it came from you. It came from all the people's trips, all the people's preferences, and none of them is the same as you. So the most important planning move I know is subtraction. Before you just run with that long list, look at what's on the plan and ask yourself honestly, which of these is here because I actually want it? And which one is here because I think I should? And then take the shoes out. It's as simple as that. If you don't care about a landmark, why do you need to go see it? It's gonna take a few hours out of your life when you could be doing something else that you enjoy. That's actually being bad company with yourself because you're busy performing a trip instead of being in the one that you actually want. Researchers also looked at how people try to improve things, and they found that we almost always reach for something to add. Guilty? Like that definitely resonates with me. And when we do this, we overlook that taking something away might actually make the whole thing better. We're just wired to add. So subtracting does take intention, maybe even a little bit of courage. And most of us need practice at this. And this isn't only about going on a big trip. I was in Krakow last weekend for work and I had one free evening. Now I'd been there years before, and basically I was there for a weekend that got rained out. So I don't have a lot of memories of the place. So you can imagine that should showed up. Okay, Damian, download a guide, go exploring, make the most of this beautiful city. It is seductive because I almost did exactly that. But I had had a busy week at the conference, and what I actually wanted was to relax and go to bed. Okay. If I'm honest, what I wanted was a sauna and a spa. I tend to look in Europe for hotels that have those features. But my hotel was booked by work and it did not have that. So I had to make do. I made do with a face mask, a couple of episodes of a Korean drama, a book, and then I went to bed. The next evening, when I was going to the closing event for the conference, I did walk around a bit. I walked on my way to the venue and just got to see some of the beauty of the city around dusk. If I'd spent hours exploring, that would have been me performing a trip that I really didn't have the energy for. I'd had a small episode of Funny Belly, and so I needed rest before anything else. Taking things away, the shoots, gave me the space for that rest. Now I know that subtracting feels uncomfortable because it can feel like you're being lazy or like you're going to miss out. Or maybe you think you're gonna get home and somebody will ask you, hey, did you see such and such famous thing? And you'll have to say, No, I didn't. But planning, again, it is not logistics. Logistics is booking the flight and sorting the hotel. But designing your trip is deciding what is it for, and then letting the other choices follow from that. And when you design your trip around what you actually want, you're not being lazy. You're the one who comes home at the end of the trip having actually enjoyed it. Now, this works with any budget, by the way. Designing for the real you isn't about spending more. For me, the afternoon tea is my version. Yours might be a walk that costs nothing. Or it could be a quiet morning sitting on a balcony overlooking a square with a coffee you love. Now, when I speak to women, I hear a lot that they're worried they're gonna be bored or lonely by themselves. Does that ever come up for you? Maybe you think that a trip is better with other people, and a solo trip is somehow a lesser version. Maybe you think that a solo trip is the trip you take when you can't get anyone to come. Okay, maybe that is true sometimes. But at times a solo trip is just a gift for myself. I'm going to London next weekend, and I have a path itinerary, not because I'm going to see Big Ben and the things and all of these other things that are very iconically British. But I have a path schedule because I'm going to get my hair done and I'm meeting my sister for lunch, and I may meet a friend for dinner, and I'm going to walk around. My version of a London weekend could be very different than yours. I've also been to London with people where we've done some sightseeing or where we have gone to see a show. I'm not trying to tell you that a trip alone is the same as a trip with somebody else. It could be, but often it isn't. A trip on your own is different from a trip with people you love. But different doesn't mean worse. Neither of these is necessarily better. I think there's a space for each of them. Years ago when I was in New Orleans, I went to Preservation Hall on my own. And I was smiling just thinking about it because the talent of the musicians was amazing. I don't even know anything about jazz, and I have a smile on my face. I didn't need anyone next to me for that to be an incredible experience. And on that same trip, I met two people through the couchsurfing app. Whatever happened to that app? What do people use now to meet folks when you travel? But anyway, I met these two ladies on couchsurfing, and then I met a guy on a plantation tour. And I must have connected everybody because next thing I knew, there was a plan to go to see the Rebirth Brass band. Now, I didn't know anything about them. But I learned that there were this Grammy award-winning band that plays at a club on Tuesday nights. I am not a night owl. So I almost didn't go. I was actually quite tired as well because there was a bit of a time difference. I think I was living in Sudan at the time. But it was a chance to spend time with people who seemed really nice and to do something that I wouldn't typically do. So I remember getting ready for bed and thinking, wait a minute, I actually do want to see this band play. I think that it would be quite a memorable experience. And I do like these people that I've met. We've had great conversation today. I would like to spend a bit more time with them. So instead of getting ready for bed, I got dressed and I went out. We were a group of four people from all over. One of them lived in California, the other one lived in New York, and the third was from France. New friends can be great when you travel alone. And what it takes is a little bit of vulnerability, but it also is showing curiosity when you meet people, being friendly, asking questions. That's the thing about traveling on your own. You have options. You can decide that you're spending time with yourself, but within your own boundaries, or you can decide that you're spending time with yourself in an open way, allowing other people close. You get to choose when do you want to be alone and when do you want to say yes to that late night show that your new friends are going to. If you think that you're going to be lonely during solo travel, you're assuming that you have to be solo the whole time. And you don't. But to be fair, it does take a bit of effort. Staying in a hostel gives you very different access to people to hang out with compared to staying in a five-star hotel, for example. And going on a group tour gives you another opportunity to be social and to make temporary or even lifelong friends. So again, the themes of logistics and design play a part here. So when you plan a solo trip, you don't plan to fill every hour so you never have any time alone with yourself. You plan so that being alone with yourself is something that you actively look forward to, that you enjoy. And those might change over time. So I'll tell you two things I do now that I didn't used to. Because I think they'll show you what designing for the real you right now looks like in practice. The first is the hop-on-hop off bus. You've probably seen them in different cities. They're those tourist buses that loop the city. Now I'll tend to take one. And sometimes I don't even hop off. I'll just ride it because I don't necessarily want to visit all the sites. But I want a sense of the city, the shape of it. Where's the river? What are the old parts? What's the history? And the bus is a very convenient way for me to get that overview. And then me from years ago would have felt the need to stop at every stop because I'd paid for it or because that's what the bus is for. And now, sometimes I just ride and I look, and that's the whole thing. The second is buying magnets. I used to never buy then because I was always thinking about my next move. There was always this next thing, a next stop, a next plan. And I thought that the magnet was clutter that I didn't have to carry. But at some point I've decided to delight in the moment instead. So now I buy the magnet. Even if I only enjoy it for a few days, that's okay. It can find a new home later if it needs to. But I want to live my life, not deferring pleasure for later. I want to feel the things that come up. It's a little thing, buying magnets, but it's a big shift. When I look back, the cost of all of my next move thinking was taking time to savor. Now, don't get me wrong, I had a lot of amazing experiences. I remember many of them with warmth, but I said the value was in more, more, more, the next thing, the next stop, fitting in as much as I possibly could. My theme song back then would probably have been, I can't get no satisfaction, honestly. Because that's exactly what more, more, more gives you. You're always already onto the next thing before you even land or before you even finish the thing you're in in the moment. And now I'd rather have the magnet. And I'd rather have the bust I don't get off. And I'll take the afternoon that I can actually savor without going to five more sites that I just rush straight through, without checking my watch every second to stay on schedule. Because when you imagine designing a trip around yourself, it can sound grand, like you need to know some big truth about what you want. This is not it, Bray Love. We're not searching for meaning. We're getting to know ourselves and what delights us and use that in our everyday lives. So don't make this bigger than it needs to be. It can be as simple as getting on that bus and seeing the city without getting off it. It can be as simple as buying a magnet or whatever it is that will help you get back in touch with those memories and remember the experiences that you had. It's a hundred small yeses to yourself. Permission for the thing you want, even when everybody else has a different opinion or a different option. This is how you learn, this is how you convince yourself that your preferences do count. Now you know I have an invitation for you this week. Look at your next planned trip or the trip you've been thinking about in your head. What's one thing that's in your plan, or what's one thing that you're thinking about because you think it should be there? Maybe there's a famous landmark that comes up for you, but you don't actually want to stand in line for it. Or somebody who's gone has told you about a walking tour, but you don't like to walk. You can do this exercise even if you're going on a trip with somebody else. In that case, you can already practice discovering and honoring your wants. So that early morning activity that leaves at 6 a.m., do you really want to do it? Take one thing off that you really don't want to do. And if you want, put something else in its place. Or leave it empty and see what comes up. Just notice how you feel about the swap. Taking one thing off matters more than adding 10 good ideas. Because adding is the easy thing. We'll do that on autopilot. Subtracting is harder, and it is the opportunity to make the trip yours, to make your life yours, really. So when you make that one swap, notice what happens in you. I want to invite you to be curious and to show up for yourself with tenderness. Because designing a trip around the real you is really a way of getting curious about who is she? That young girl you were, the one with all the dreams, the woman you've become, who've learned so much along the way. Who are they? In solo travel, we get a chance to meet all of ourselves. So that's the invitation for the week. One should remove one thing you actually want, put in its place or leave it empty. And pay attention to what happens when you look at the trip again, when you look at that activity again. I think you'll feel that the plan is a bit lighter. I think you'll feel a little bit more excitement. If you want to think about this within the context of a whole trip and not just one swap, that's exactly what the solo trip decision workshop is. It's one hour. You bring the trip you've been designing in your head, and we look at how you would design it around the woman you actually are so that you walk out with a plan that fits you. The next workshop is on June 20th, and the link is in the show notes. So let me leave you with this. The reason I want you to think about planning a trip this way, designing a trip around the real you, is because it's not really about the trip. Planning a trip for who you actually are is one of the kindest things you can do for yourself. You sit down with your own preferences, whether you want a slow morning or a fast afternoon, whether you want to get on a bus and not get off. Instead of apologizing for them, you get to build a whole trip that honors them. So be a little tender with yourself when you sit down to plan. Get curious about what is it that you actually want, what would actually delight you. And think about it in this season, in this moment. Design comes from that place. If something in this episode landed for you, come find me in the community at freedomlookslikevist.com forward slash community. I'd love to hear what you swapped. Thanks for spending this time with me. If something in this episode resonated, choose one small action and try it in whatever way feels doable for you. And if you want the simplest place to start, come to the solo trip decision workshop and we'll design your trip around the woman you actually are.